Jennifer F. Shepley, CFP®, is a financial professional based in Massachusetts, with licensing across multiple states. She specializes in family and small business insurance, retirement income planning, and long-term care solutions. Her journey into the industry was a blend of serendipity and family tradition, shaped by the legacy of her father, who founded his insurance practice in 1959.
“My dad was set on having ‘Shepley and Sons,’ but life had other plans,” Jennifer shares with a smile. At the time, she was a dedicated teacher, contemplating her next steps. “I was going to take a year off to work with Habitat for Humanity, but my dad had other ideas. He told me, ‘Shepley and Sons isn’t working out, but I think you should join the business.’”
Intrigued by her father’s description of the profession as akin to teaching and coaching, Jennifer took the leap in 1997. She passed her licensing exams, joined the family practice, and never looked back.
A Lifelong Commitment to Professionalism
Jennifer’s father instilled in her the belief that professionals should always join their professional organizations, and Jennifer took that advice to heart. She became a NAIFA member in 1997 and immediately took on a leadership role as secretary for the Massachusetts chapter. Over the past 27 years, Jennifer has remained deeply involved in NAIFA, leveraging its vast network, resources, and opportunities for professional development.
"NAIFA has been instrumental in my career,” Jennifer explains. “It’s more than just an organization—it’s a community. I’ve gained so much from the relationships, the mentoring, and the educational programs it provides. It keeps me connected to industry trends and helps me navigate the changes in regulations and client needs.”
Through NAIFA, Jennifer has built strong connections with other professionals, which has enriched both her personal growth and her business practice. "The camaraderie is incredible. Whether it's exchanging ideas with colleagues at a local event or attending national conferences, being part of NAIFA means you’re never alone in this industry. You always have a network of peers who understand the challenges and celebrate the successes with you."
Education and Professional Growth
In addition to her steadfast dedication to NAIFA, Jennifer has pursued extensive professional development. “My dad believed in staying educated, and so do I,” she says. She earned her LUTCF designation within three months of joining the industry, followed by her CFP®. She later added the RICP® designation to her credentials, ensuring she stays ahead in a constantly evolving field.
NAIFA’s emphasis on education has aligned perfectly with Jennifer’s personal values. “One of the things I love about NAIFA is its commitment to lifelong learning. Whether it’s webinars, in-person workshops, or certification programs, NAIFA ensures we have the tools and knowledge to best serve our clients.”
A Legacy of Excellence
Jennifer’s journey from teaching to financial services exemplifies adaptability, commitment, and the importance of family values. She has transformed her father’s vision into a thriving career that serves individuals, families, and small businesses with professionalism and care.
Reflecting on her 27 years as a NAIFA member, Jennifer emphasizes how the organization has been a cornerstone of her professional journey. “NAIFA’s mission of advocacy, education, and community resonates deeply with me. It’s given me the platform to grow as a professional while giving back to an industry that’s been so rewarding.”
As Jennifer celebrates nearly three decades in the industry, her dedication to clients, education, and professional integrity continues to honor the legacy her father began in 1959. Her commitment to NAIFA is an enduring testament to the value of professional associations in fostering excellence and success.
Jennifer F., Shepley, LUTCF, CFP
55 County Road POB 748
Mattapoisett, MA 02739
(508) 322-3210
Registered Representative and Financial Advisor of Park Avenue Securities LLC (PAS). OSJ: 160 GOULD STREET, SUITE 310, NEEDHAM MA, 02494, 781-4494402. Securities products and advisory services offered through PAS, member FINRA, SIPC. The Bulfinch Group is not an affiliate or subsidiary of PAS or Guardian. Life insurance offered through The Bulfinch Group Insurance Agency, LLC, an affiliate of The Bulfinch Group, LLC. The Bulfinch Group, LLC is not licensed to sell insurance. CA Insurance License Number - 0D03795. 7472277.1 Exp 12/26